(E)-1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-but-2-en-1-one | 235094-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (E)-1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-but-2-en-1-one
• 英文别名: (E)-1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(phenylselanylmethyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]but-2-en-1-one
• CAS: 235094-17-4
• 化学式: C₂₂H₃₁NO₂Se
• 分子量: 420.454
• InChiKey: VUZRBHUOPRAORX-UAAXDJHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-but-2-en-1-one 在 lithium aluminium tetrahydride 、 三氯化铝 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.17h， 生成 (3'R)-8-(3'-ethylpyrrolidinyl)menthol
  参考文献：
  名称：

  A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol

  摘要：

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.

  DOI：

  10.1021/jo981693t
• 作为产物：
  描述：

  2-丁烯酰氯 、 2-(phenylseleno)methylperhydro-1,3-benzoxazine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到(E)-1-((2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-phenylselanylmethyl-hexahydro-benzo[e][1,3]oxazin-3-yl)-but-2-en-1-one
  参考文献：
  名称：

  A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol

  摘要：

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.

  DOI：

  10.1021/jo981693t

文献信息

• A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol
  作者：Celia Andrés、Juan P. Duque-Soladana、Rafael Pedrosa

  DOI：10.1021/jo981693t

  日期：1999.6.1

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.